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Acetyl chloride → 1-[2-(3-Ethyl-5-methyl-1,2-oxazol-4-yl)-1H-indol-3-yl]ethan-1-one

HRID 358404
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HRID 358404 반응식
[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:17])[O:5][N:4]=1)[CH3:2].[C:18](Cl)(=[O:20])[CH3:19]>FC(F)(F)S([O-])(=O)=O.[Ag+].C(Cl)Cl>[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:17])[O:5][N:4]=1)[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 6367Acetyl chlorideHCID 130386862-(3-Ethyl-5-methyl-1,2-oxazol-4-yl)-1H-indole

생성물 1

HCID 128514531-[2-(3-Ethyl-5-methyl-1,2-oxazol-4-yl)-1H-indol-3-yl]ethan-1-one

시약·촉매·용매 2

HCID 76223Silver(I) trifluoromethanesulfonate촉매HCID 6344Dichloromethane용매2회

실험 절차

A solution of 33.5 g. (0.148 mole) of 2-(3-ethyl-5-methyl-4-isoxazolyl)-indole in 450 ml. methylene chloride is treated by the portionwise addition of 41.8 g. (0.163 mole) of silver trifluoromethanesulfonate. The resulting suspension is then treated by the dropwise addition of 12.8 g. (0.163 mole) of acetyl chloride in 50 ml. methylene chloride. The temperature rises to 35° C. during the addition. After the addition is complete the mixture is stirred at room temperature for 4 hours and then filtered. The filtrate is washed with 150 ml. 2N sodium hydroxide, water and 2N sodium hydroxide dried over anhydrous magnesium sulfate and evaporated in vacuo to given an oil. The oil is crystallized from ether to give 2-(3-ethyl-5-methyl-4-isoxazolyl)-3-acetyl indole, m.p. 170°-173° C.

후처리

  1. additionThe resulting suspension is then treated by the dropwise addition of 12.8 g
  2. additionThe temperature rises to 35° C. during the addition
  3. additionAfter the addition
  4. filtrationfiltered
  5. washThe filtrate is washed with 150 ml
  6. dry with material2N sodium hydroxide, water and 2N sodium hydroxide dried over anhydrous magnesium sulfate
  7. customevaporated in vacuo
  8. customThe oil is crystallized from ether

출처 및 근거

ORD 기록
ord-bcdf2fbf26a547f4bfe93c44485e73ca
출처 데이터셋
uspto-grants-1984_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04467096

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